Good morning, sunshine! ☀️ Let’s get you ready for the best, most fun-filled day during Christmastime in Chicago! Set those alarms for 10 a.m.! Beauty sleep is key, so there’s no need to stress. Put on a cute outfit, grab something to eat, and hop in that Uber, train, or bike. Doesn’t matter how you get there, but let’s arrive at 11 a.m.!
After all that traveling, I’m sure you are exhausted and need a pick-me-up. Let’s make our way over to Chicago’s most aesthetic (and delicious) coffee shop: Ralph’s Coffee! ☕ My recommendation? The gingerbread latte. Whether you like your coffee hot or iced, grab it quickly before we make our way to the Magnificent Mile.
On the way to our next activity, let’s take some time to shop along Chicago’s Mag Mile! 🛍️ Some great stores to stop by, especially for that Christmas feeling, are Tiffany & Co., Nordstrom, and Bloomingdale’s. You might just be able to find the perfect gift on your way. As you shop, make your way down to Maggie Daley Park, which makes a 30-minute walk feel like a breeze.
At this point, it should be right around 2 p.m. Lucky for you, the Maggie Daley Park Ice Skating Ribbon ⛸️ has an open skate session from 2–4 p.m. I recommend booking your tickets online, so that they are slightly cheaper. Weekday tickets are $17, and weekends are $21. If you’re a pro and bring your own skates, it’s only $5. While you experience the beautiful views of Chicago on ice, you’ll find the time just slipping past.
As your session ends at 4 p.m., you can (sadly) retire the skates and walk over to Millennium Park. As a true tourist, you’ll of course stop to see the Bean (and take a few pictures). Then, you’ll make your way over to the Millennium Park Christmas Tree! 🎄 One perk of being stuck in a dark Chicago winter is getting to see the tree lit up so early…
At this point, I’m sure you are absolutely starving — it’s been an active day! Now here comes the heavy hitter: restaurant recommendations. 😋 Now, I don’t want to make you go too far, since I think there’s been enough walking for today. I’m going to go from most expensive to least expensive. Starting off, if you really want to make this day worth it with the full Chicago Christmas experience, go to Cindy’s Rooftop! 🦞 Located on the roof of the Chicago Athletic Association Hotel, it offers fantastic views of the city and Millennium Park. The menu is extensive, but they are especially known for their delicious seafood. Another great option for an even more reasonable price is Miller’s Pub! 🍔 Serving classic American dishes, it has a great vintage feel that will surely elevate your experience. Now, if you are looking for a classic Chicago day, make your way over to Giordano’s. 🍕 This is your classic deep-dish Chicago-style pizza at a great price. Lastly, if you don’t want to break the bank and are looking for a really quick stop, check out Shake Shack or Raising Cane’s right on Michigan Ave!
Time to get your energy back up, because we’re going on the road again! Whether it’s Uber or CTA, make a quick trip over to Wrigleyville! Hoping to arrive around 7 p.m., we are wrapping up our Christmas day in Chicago by making a visit to the Christkindlmarket! 🍫 There is a location downtown; however, the Wrigleyville one is usually much less crowded. Take your time walking around, looking at the decorations, and maybe buying some tasty German treats!
At this point, it may be running a little late, but if you are a night owl, there is plenty to do in Wrigleyville! You can walk around and see the nightlife, look at the decorations, or maybe grab a dessert. Other than this, your night has come to an amazing end! You shopped, ate fantastic food, ice skated, saw beautiful Christmas lights, and experienced the wonders of Chicago! Now you can head back home, make some hot chocolate, and watch a Christmas movie 🧑🎄 (My personal recommendation is Elf). Whether you spend this day on a solo trip, with family, friends, or that special someone, I guarantee it will make your holiday season so much better!
Finally, just a couple more tips and tricks to help the day go so much smoother! ✅ Always think ahead for any sit-down restaurant, especially during the holiday season. Make those reservations! This is extremely important if you don’t want to go hungry! Along with that, plan accordingly. This is based on weather, traffic, and the overall busiest days of the week. Try to avoid weekends if possible, Monday-Thursday are the best days to attend! If a weekend is a must, definitely go on Sunday. Keep in mind, however, that the Christkindlmarket does close at 7 p.m. on Sundays instead of 9! Aside from that, just stick to a schedule and have fun! Happy holidays!
